Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester

Base Information

Chemical Name:Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester
CAS No.:475291-43-1
Molecular Formula:C₂₈H₄₃NO₁₀S
Molecular Weight:585.716
Hs Code.:

Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester

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Chemical Property of Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester

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Technology Process of Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester

There total 18 articles about Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 124-63-0
methanesulfonyl chloride

: 397870-73-4
tert-butyl N-[(E,2S,3R,4R,5S)-2-benzyloxymethyl-8-hydroxy-1,3:4,5-bis(isopropylidenedioxy)oct-6-en-2-yl]carbamate

: 475291-43-1
Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 25 ℃; for 0.333333h;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 100-39-0
benzyl bromide

: 475291-43-1
Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 88 percent / CsF / dimethylformamide / 13 h / 80 °C

2.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 0 °C

3.1: 98 percent / toluene / 17 h / 100 °C

4.1: 73 percent / DIBAL-H / toluene / 3 h / -78 °C

5.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 89.4 mg / K₂CO₃ / xylene / 156 h / 140 °C

7.1: ozone / CH₂Cl₂ / 0.33 h / -78 °C

7.2: Me₂S / CH₂Cl₂ / 2.5 h / 0 °C

8.1: 93 percent / Zn(BH₄)2 / diethyl ether / 1 h / 25 °C

9.1: aqueous HCl / tetrahydrofuran / 3 h / 25 °C

10.1: benzoic acid / CH₂Cl₂ / 2.5 h / 25 °C

11.1: 641 mg / camphorsulfonic acid / benzene / 13 h / 50 °C

12.1: DIBAL-H / toluene / 4 h / -78 °C

13.1: 223 mg / NaHCO₃ / methanol / 12 h / 25 °C

14.1: triethylamine / CH₂Cl₂ / 0.33 h / 25 °C

With hydrogenchloride; zinc(II) tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; benzoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; xylene; benzene; 2.1: Swern oxidation / 6.1: Overman rearrangement;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 104487-62-9
1,2-O-isopropylidene-3-O-methoxymethyl-α-D-glucofuranose

: 475291-43-1
Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 88 percent / CsF / dimethylformamide / 13 h / 80 °C

2.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 0 °C

3.1: 98 percent / toluene / 17 h / 100 °C

4.1: 73 percent / DIBAL-H / toluene / 3 h / -78 °C

5.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 89.4 mg / K₂CO₃ / xylene / 156 h / 140 °C

7.1: ozone / CH₂Cl₂ / 0.33 h / -78 °C

7.2: Me₂S / CH₂Cl₂ / 2.5 h / 0 °C

8.1: 93 percent / Zn(BH₄)2 / diethyl ether / 1 h / 25 °C

9.1: aqueous HCl / tetrahydrofuran / 3 h / 25 °C

10.1: benzoic acid / CH₂Cl₂ / 2.5 h / 25 °C

11.1: 641 mg / camphorsulfonic acid / benzene / 13 h / 50 °C

12.1: DIBAL-H / toluene / 4 h / -78 °C

13.1: 223 mg / NaHCO₃ / methanol / 12 h / 25 °C

14.1: triethylamine / CH₂Cl₂ / 0.33 h / 25 °C

With hydrogenchloride; zinc(II) tetrahydroborate; oxalyl dichloride; camphor-10-sulfonic acid; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; benzoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; xylene; benzene; 2.1: Swern oxidation / 6.1: Overman rearrangement;
DOI:10.1246/bcsj.75.1927